EP1731035B1 - Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen - Google Patents

Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen Download PDF

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Publication number
EP1731035B1
EP1731035B1 EP06016907A EP06016907A EP1731035B1 EP 1731035 B1 EP1731035 B1 EP 1731035B1 EP 06016907 A EP06016907 A EP 06016907A EP 06016907 A EP06016907 A EP 06016907A EP 1731035 B1 EP1731035 B1 EP 1731035B1
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Prior art keywords
diol
vicinal
group
vicinal diol
pests
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English (en)
French (fr)
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EP1731035A1 (de
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John Campbell
Andrew Carver
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EctoPharma Ltd
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EctoPharma Ltd
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Priority to EP10179702A priority Critical patent/EP2311319A1/de
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Publication of EP1731035B1 publication Critical patent/EP1731035B1/de
Priority to CY20111101212T priority patent/CY1112155T1/el
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/002—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits
    • A01N25/006—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits insecticidal
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions

Definitions

  • This invention relates to a method of controlling arthropod pests which comprises applying an effective amount of at least one vicinal diol R (OH) 2 , to the locus of the pests or their ova, whereby the pests are killed or rendered moribund, wherein said vicinal diol is a 1, 2 diol and is selected from the group consisting of diols wherein R represents a linear aliphatic hydrocarbyl chain, with the proviso that the backbone of that chain comprises from 8 to 14 carbon atoms, wherein the method is not for treatment of the human or animal.
  • R represents a linear aliphatic hydrocarbyl chain
  • the pesticide in either case is ecologically-friendly (i.e. biodegradable).
  • An object of the present invention is to provide alternative pesticidal agents that will obviate or mitigate at least some of the drawbacks of currently commercially available products.
  • it is an object to provide a method of control of arthropod, as disclosed in present claim 1.
  • the compound has at least one hydrocarbyl chain of length n+2 atoms, wherein the value of n is from 6 to 12 carbons, and the vicinal hydroxyls occupy a terminal position, having hydroxyls at 1,2-positions such that the diol forms a head group with a lipophilic tail. Differing activities are observed with changes in n value. This leads to preferences amongst them and differences in activity for lower alkyl groups in comparison with higher alkyl groups (C 6 and above). Compounds wherein n has a value of from 6 to 12 inclusive are of particular interest currently.
  • Such diols are chiral in nature with, for example, the second carbon being a chiral centre in the case of 1,2 diols.
  • a racemic mixture is usefully employed in the present invention but single optical isomers (enantiomers), or mixtures containing a preponderance of one or more particular optical isomer(s) can also serve the purposes of the invention.
  • enantiomers of 1,2-decanediol have been shown to be effective against lice in comparable fashion to the racemic mixture whose results are tabulated hereinafter.
  • 1,2-alkyldiols for the control of bacterial infection has already been shown.
  • Pugliese US patent 4 049 830 teaches the application of 1,2-alkyl diols for the sterilisation of bovine teats as a prophylactic treatment for bacterial bovine mastitis.
  • Greff US patent 6 123 953 teaches the use of 1,2-diols for generalised topical application in the control of bacteria that cause skin ailments including mastitis, acne and dandruff.
  • Agostini and Cupferman European patent application EP 0 935 960 A1 teach cosmetic formulation containing an 1,2-alkyl diol as an antibacterial agent.
  • Airs in GB 687 850 has taught the use of certain vicinal diols as insect repellents together with known nonsolvent insecticides.
  • the potential for the application of vicinal diols as the active ingredient in the control of pests by killing them or their ova has not heretofore been considered.
  • Lover and Singer et al ( United States patent 4 368 207 ) teach the use of a range of monohydric alcohols against lice, their ova, and mites.
  • Lover and Singer et al teach the use of non-vicinal, particularly 1,3 diols, in United Kingdom patent GB 1 604 856 . That patent suggests such compounds for the control of ectoparasites and their ova.
  • vicinal diols as disclosed in the claims, have surprisingly enhanced pesticidal properties in comparison with mono-ols or non-vicinal diols and may be used to kill a wide range of common arthropod pests, notably arachnids, such as ticks and mites, and insects, such as flies, cockroaches, silverfish and lice, and ovicidal effects can be demonstrated. Moreover these are found to be biodegradable, and eminently suitable as valuable pesticides for a wide variety of uses and applications.
  • formulations that are suitable for contact application of such vicinal diols or their derivatives, comprising at least one such vicinal diol in a physiologically tolerable carrier, for the control of specific pest-induced ailments of humans and animals, including head- or body-louse infection, carpet mite infestation, sheep-scab mite infection and blow-fly strike.
  • the formulations will comprise compositions of the preferred vicinal diols alone or in combination, together with suitable auxiliaries as required, with a carrier adapted to deliver an effective amount of the vicinal diol(s) to the locus of a pest infestation.
  • the carrier will usually be selected with a view to prolonging contact with the target pest.
  • the carrier may be a finely divided solid or a liquid, and may be selected from powder, resins, and aqueous or organic fluids. Therefore, a suitable formulating aid may be selected from liquid vehicles, solid carriers, auxiliaries, emulsifiers, dispersants, resins, gums, adherents, diluents and extenders.
  • the pesticidal composition may be suitably prepared for delivery in a formulation selected from a solution, a dispersion, an emulsion, a dusting powder, a paste, an aerosol, a cream, a foam, a coated substrate e.g. tacky paper, a pellet or block e.g. as in a bait for a trap.
  • a physiologically benign or tolerable carrier when the pest is to be combated directly upon a live host, and may select such carriers from pharmaceutically acceptable carriers, especially those intended for topical application, to form creams, gels, pastes and ointments, aerated (foam/mousse) compositions or dusting powders e.g. talc.
  • compositions provided by this invention are demonstrated firstly with regard to the human body louse ( Pediculus humanus ), using vicinal diols in tests according to accepted industry protocols.
  • Tables 1 and 2 The special value and unique nature of vicinal diols is illustrated in Tables 1 and 2 wherein the LC 50 values, measured in tests against lice, for a range of diols and mono-ols are tabulated.
  • Table 1 shows the surprising potency of the vicinal diols in comparison to 1,3 and other non-vicinal diols. For example 1,2-decanediol is significantly superior to 1,3-decanediol and the benefit of the vicinal compounds is apparent in the Table for all the examples of chain length shown.
  • Table 2 shows similar superiority of the vicinal diols over mono-ols and some triols.
  • the best mono-ol tested has only 36% of the potency found for 1,2-decanediol.
  • the superior potency of the vicinal diols provides the benefit that they can provide effective control of a pest even when applied in a less than ideal manner to the target organisms.
  • a yet further benefit of these compounds is that they have been shown to be readily metabolised by common soil bacteria, derived from several different locations, and so will biodegrade readily when dispersed in the environment.
  • 1,2 diols have pediculicidal activity, to the extent that C 4 to C 16 diols are active, and those from C 8 to C 14 are preferred, with the most preferred being 1,2-octanediol, 1,2-decanediol and 1,2-dodecanediol.
  • Figure 2 demonstrates a further a beneficial property of the subject matter of the invention, namely the inhibition of egg laying, an important feature in that the life cycle of the target organism is interrupted when egg laying is inhibited or stopped. This is observed by considering the graphic illustration of efficacy of a range of diols which shows that as diol chain length increases egg laying activity of treated lice declines substantially. 1,2-Octanediol is especially efficacious in the prevention of egg laying.
  • a further example of the use of the compounds of the present invention is shown by testing decane-1,2-diol against house flies in a standard industry protocol for insecticides. More than 80% mortality was observed after 24 hours contrasting with decane-1,10-diol which did not exhibit insecticidal activity.
  • Vicinal diols are readily formulated in aqueous systems using non-toxic co-solvents such as isopropyl alcohol or by use of surfactants such as Tween®. This makes them eminently suitable for inclusion into many household or industrial, pesticidal or cleansing products. In particular they can be incorporated into pharmaceutical preparations for use on humans or animals.
  • the treatment of lice and cockroaches with formulations containing 1,2-octanediol or 1,2-decanediol is tabulated in Table 4 along with control results for the solvent systems employed. In a procedure following standard industry protocols the subject animals were immersed for a few seconds in the test formulations and blotted dry.
  • the invention will be usefully applied in dealing with pests encountered in agriculture, horticulture, human health, hygiene and veterinary medicine.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Insects & Arthropods (AREA)
  • Food Science & Technology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (19)

  1. Ein Verfahren zur Bekämpfung von Gliederfüßerschädlingen, das das Anwenden einer wirksamen Menge von mindestens einem vicinalen Diol R(OH)2 auf die Stelle der Schädlinge oder ihre Eier beinhaltet, wodurch die Schädlinge vernichtet oder in einen moribunden Zustand versetzt werden, wobei das vicinale Diol ein 1,2-Diol ist und aus der Gruppe, bestehend aus Diolen, ausgewählt ist, wobei R eine lineare aliphatische Hydrocarbylkette darstellt, mit der Maßgabe, dass die Hauptkette dieser Kette 8 bis 14 Kohlenstoffatome beinhaltet, wobei das Verfahren nicht zur Behandlung des menschlichen oder tierischen Körpers mittels Chirurgie oder Therapie und Diagnoseverfahren, die an dem menschlichen oder tierischen Körper ausgeführt werden, dient.
  2. Verfahren gemäß Anspruch 1, wobei das vicinale Diol aus einer nicht substituierten aliphatischen Hydrocarbylkette aus n + 2 Atomen in der Hauptkette darin besteht, wobei die Hydroxyle des vicinalen Diols eine Endposition belegen, wodurch die Hydroxyle des Diols und die Kohlenstoffe, mit denen sie verknüpft sind, eine Obergruppe bilden, und n eine ganze Zahl ist, die einen Wert von mindestens 6 aufweist.
  3. Verfahren gemäß Anspruch 2, wobei n einen geraden Wert aufweist.
  4. Verfahren gemäß Anspruch 1, wobei die Hydrocarbylkette teilweise ungesättigt ist.
  5. Verfahren gemäß Anspruch 1, wobei die vicinalen Diole aus der Gruppe, bestehend aus linearen aliphatischen 1,2-Diolen mit einer Kettenlänge zwischen 8 und 12 Kohlenstoffatomen, ausgewählt sind.
  6. Verfahren gemäß Anspruch 1, wobei die vicinalen Diole aus der Gruppe, bestehend aus 1,2-Octandiol, 1,2-Decandiol und 1,2-Dodecandiol, ausgewählt sind.
  7. Verfahren gemäß einem der vorhergehenden Ansprüche, wobei die Schädlinge Läuse sind und das mindestens eine vicinale Diol ein aliphatisches 1,2-Diol ist und in Kombination mit einem formulierenden Hilfsmittel, das aus der Gruppe, bestehend aus flüssigen Vehikeln, festen Trägern, Hilfsstoffen, Emulgatoren, Dispersionsmitteln, Harzen, Haftmitteln, Verdünnungsmitteln und Streckmitteln, ausgewählt ist, auf die Stelle des Läusebefalls angewendet wird.
  8. Verfahren gemäß Anspruch 7, wobei das mindestens eine vicinale Diol in einer Abgabeformulierung bereitgestellt ist, die aus der Gruppe, bestehend aus einer Lösung, einer Dispersion, einer Emulsion, einem Pudermittel, einem Gel, einer Paste, einem Aerosol, einer Creme, einem Schaum, einem beschichteten Substrat, einem Kügelchen und einem Block, ausgewählt ist.
  9. Verfahren gemäß Anspruch 7, wobei das mindestens eine vicinale Diol eine wirksame Menge an 1,2-Decandiol umfasst.
  10. Verfahren gemäß Anspruch 7, wobei das mindestens eine vicinale Diol eine wirksame Menge einer Kombination aus 1,2-Octandiol und 1,2-Decandiol umfasst.
  11. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei das mindestens eine vicinale Diol ein aliphatisches 1,2-Diol ist, die Schädlinge Fliegen sind und das Verfahren die Anwendung des mindestens einen vicinalen Diols in Kombination mit einem formulierenden Hilfsmittel, das aus der Gruppe, bestehend aus flüssigen Vehikeln, festen Trägern, Hilfsstoffen, Emulgatoren, Dispersionsmitteln, Harzen, Haftmitteln, Verdünnungsmitteln und Streckmitteln, ausgewählt ist, auf die Stelle eines Befalls beinhaltet.
  12. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei das mindestens eine vicinale Diol ein aliphatisches 1,2-Diol ist, die Schädlinge Fliegen sind und das Verfahren das Heranführen eines Köders oder einer Falle, behandelt mit dem mindestens einen vicinalen Diol, in Kombination mit einem formulierenden Hilfsmittel, das aus der Gruppe, bestehend aus flüssigen Vehikeln, festen Trägern, Hilfsstoffen, Emulgatoren, Dispersionsmitteln, Harzen, Haftmitteln, Verdünnungsmitteln und Streckmitteln, ausgewählt ist, an die Stelle eines Befalls beinhaltet.
  13. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei das mindestens eine vicinale Diol ein aliphatisches 1,2-Diol ist, die Schädlinge Milben sind und das Verfahren die Anwendung des mindestens einen vicinalen Diols in Kombination mit einem formulierenden Hilfsmittel, das aus der Gruppe, bestehend aus flüssigen Vehikeln, festen Trägern, Hilfsstoffen, Emulgatoren, Dispersionsmitteln, Harzen, Haftmitteln, Verdünnungsmitteln und Streckmitteln, ausgewählt ist, auf die Stelle eines Befalls beinhaltet.
  14. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei das mindestens eine vicinale Diol ein aliphatisches 1,2-Diol ist, die Schädlinge Schaben sind und das Verfahren die Anwendung des mindestens einen vicinalen Diols in Kombination mit einem formulierenden Hilfsmittel, das aus der Gruppe, bestehend aus flüssigen Vehikeln, festen Trägern, Hilfsstoffen, Emulgatoren, Dispersionsmitteln, Harzen, Haftmitteln, Verdünnungsmitteln und Streckmitteln, ausgewählt ist, auf die Stelle eines Befalls beinhaltet.
  15. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei das mindestens eine vicinale Diol ein aliphatisches 1,2-Diol ist, die Schädlinge Schaben sind und das Verfahren das Heranführen eines Köders oder einer Falle, behandelt mit dem mindestens einen vicinalen Diol, in Kombination mit einem formulierenden Hilfsmittel, das aus der Gruppe, bestehend aus flüssigen Vehikeln, festen Trägern, Hilfsstoffen, Emulgatoren, Dispersionsmitteln, Harzen, Haftmitteln, Verdünnungsmitteln und Streckmitteln, ausgewählt ist, an die Stelle eines Befalls beinhaltet.
  16. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei der Schädling aus der Gruppe, bestehend aus Pediculus humanus, Dermatophagoides pteronyssinus, Musca domestica, den Blattidae, Blatella Germanica und Periplaneta Americana, ausgewählt ist, und das Verfahren das Heranführen einer Zusammensetzung, die als Wirkstoff ein vicinales Diol enthält, das aus der Gruppe, bestehend aus 1,2-Octandiol, 1,2-Decandiol, 1,2-Dodecandiol und Kombinationen davon, ausgewählt ist, an die Stelle eines Befalls des Schädlings beinhaltet.
  17. Verfahren gemäß Anspruch 16, wobei das Diol als eine Formulierung, die aus der Gruppe, bestehend aus einer Lösung, einer Dispersion, einer Emulsion, einem Pudermittel, einem Gel, einer Paste, einem Aerosol, einer Creme, einem Schaum, einem beschichteten Substrat, einem Kügelchen und einem Block, ausgewählt ist, herangeführt wird.
  18. Verfahren gemäß einem der vorhergehenden Ansprüche, wobei das mindestens eine vicinale Diol als eine Zusammensetzung verabreicht wird, die im Wesentlichen aus dem mindestens einen vicinalen Diol und mindestens einem Hilfsstoff besteht.
  19. Verfahren gemäß Anspruch 18, wobei die Zusammensetzung ferner einen Träger beinhaltet.
EP06016907A 2001-03-02 2002-02-28 Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen Expired - Lifetime EP1731035B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP10179702A EP2311319A1 (de) 2001-03-02 2002-02-28 Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen
CY20111101212T CY1112155T1 (el) 2001-03-02 2011-12-06 Παρασιτοκτονα με βαση τις vic-διολες

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0105229.9A GB0105229D0 (en) 2001-03-02 2001-03-02 Pesticides
EP02702490A EP1377162B1 (de) 2001-03-02 2002-02-28 Verwendung von vicinalen 1,2-Diole zur Befämpfung von Anthropoden

Related Parent Applications (2)

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EP02702490.0 Division 2002-02-28
EP02702490A Division EP1377162B1 (de) 2001-03-02 2002-02-28 Verwendung von vicinalen 1,2-Diole zur Befämpfung von Anthropoden

Related Child Applications (1)

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EP10179702.5 Division-Into 2010-09-24

Publications (2)

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EP1731035A1 EP1731035A1 (de) 2006-12-13
EP1731035B1 true EP1731035B1 (de) 2011-09-14

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EP06016907A Expired - Lifetime EP1731035B1 (de) 2001-03-02 2002-02-28 Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen
EP10179702A Withdrawn EP2311319A1 (de) 2001-03-02 2002-02-28 Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen
EP02702490A Expired - Lifetime EP1377162B1 (de) 2001-03-02 2002-02-28 Verwendung von vicinalen 1,2-Diole zur Befämpfung von Anthropoden

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EP10179702A Withdrawn EP2311319A1 (de) 2001-03-02 2002-02-28 Schädlingsbekämpfungsmittel auf Basis von vicinalen Diolen
EP02702490A Expired - Lifetime EP1377162B1 (de) 2001-03-02 2002-02-28 Verwendung von vicinalen 1,2-Diole zur Befämpfung von Anthropoden

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US (3) US7510723B2 (de)
EP (3) EP1731035B1 (de)
JP (1) JP4280499B2 (de)
KR (1) KR100884922B1 (de)
CN (1) CN1306869C (de)
AT (2) ATE524066T1 (de)
AU (1) AU2002236016B2 (de)
BR (1) BRPI0207756B1 (de)
CA (1) CA2438845C (de)
CY (2) CY1107988T1 (de)
DE (1) DE60214989T2 (de)
DK (2) DK1731035T3 (de)
ES (2) ES2373050T3 (de)
GB (1) GB0105229D0 (de)
IL (1) IL157670A0 (de)
MX (1) MXPA03007804A (de)
NZ (1) NZ528113A (de)
PT (2) PT1731035E (de)
RU (1) RU2285405C2 (de)
WO (1) WO2002069707A1 (de)
ZA (1) ZA200307018B (de)

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GB0105229D0 (en) 2001-03-02 2001-04-18 Ectopharma Ltd Pesticides
DE102013223792A1 (de) * 2013-11-21 2015-05-21 Henkel Ag & Co. Kgaa Verwendung kosmetischer Zusammensetzungen für die Inaktivierung und/oder Eliminierung von Hautmilben
CN105439782B (zh) * 2015-12-14 2019-02-19 中国科学院南京土壤研究所 癸二醇作为硝化抑制剂的应用
CN109890783B (zh) * 2016-09-14 2022-06-14 基因组股份公司 1,3-脂肪二醇化合物和其衍生物

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RU2003129268A (ru) 2005-03-20
CN1306869C (zh) 2007-03-28
DE60214989T2 (de) 2007-05-10
ZA200307018B (en) 2005-05-25
HK1065221A1 (en) 2005-02-18
DE60214989D1 (de) 2006-11-09
US20090149552A1 (en) 2009-06-11
KR100884922B1 (ko) 2009-02-20
ATE340505T1 (de) 2006-10-15
WO2002069707A1 (en) 2002-09-12
ATE524066T1 (de) 2011-09-15
CN1494375A (zh) 2004-05-05
IL157670A0 (en) 2004-03-28
JP4280499B2 (ja) 2009-06-17
GB0105229D0 (en) 2001-04-18
AU2002236016B2 (en) 2007-05-24
ES2373050T3 (es) 2012-01-30
US20140357728A1 (en) 2014-12-04
US9456601B2 (en) 2016-10-04
EP1377162A1 (de) 2004-01-07
BR0207756A (pt) 2004-03-23
CY1107988T1 (el) 2013-09-04
EP1731035A1 (de) 2006-12-13
EP1377162B1 (de) 2006-09-27
BRPI0207756B1 (pt) 2015-04-14
DK1731035T3 (da) 2012-01-16
US20040091512A1 (en) 2004-05-13
US7510723B2 (en) 2009-03-31
PT1731035E (pt) 2012-01-03
ES2273998T3 (es) 2007-05-16
CY1112155T1 (el) 2015-12-09
NZ528113A (en) 2006-04-28
RU2285405C2 (ru) 2006-10-20
KR20030087007A (ko) 2003-11-12
CA2438845A1 (en) 2002-09-12
PT1377162E (pt) 2007-01-31
US8784855B2 (en) 2014-07-22
CA2438845C (en) 2012-05-08
DK1377162T3 (da) 2007-02-12
MXPA03007804A (es) 2004-11-12
JP2004525114A (ja) 2004-08-19

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